1

The Great Gatsby , F. Scott Fitzgerald (1925)

Image: Girl with red hat

Written by F. Scott Fitzgerald, one of the most iconic authors of the so-called "Lost Generation", The Great Gatsby portrays the dark side of the American dream . The protagonist, the mysterious and apparently frivolous millionaire Jay Gatsby, is obsessed with winning back a woman he loved in his youth. Set in the Jazz Age, Fitzgerald’s book raises the contradictions between the power of money and the most intimate individual aspirations.

Published in 1925, The Great Gatsby is one of the greatest masterpieces of American fiction . Since then, it has sold millions of copies all over the world, has had numerous theatrical and film adaptations, and was chosen as the best American novel of the 20th century on several occasions.

2

The Sound and the Fury , William Faulkner (1929)

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Published in 1929, The Sound and the Fury is William Faulkner's fourth novel and is considered the greatest opus of this Nobel Laureate . It chronicles the decadence of the Compsons, an aristocratic family in the American South, their secrets, and the relationships of love and hate that sustain and destroy them.

The Sound and the Fury is a profound and heartbreaking exploration of decay, despair, and loss . Faulkner's innovative narrative technique, while challenging, allows for an intimate and visceral portrayal of the characters. The novel also addresses issues of race, gender, and class with admirable narrative prowess.

3

The Old Man and the Sea , Ernest Hemingway (1952)

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The Old Man and the Sea was the last novel published by Ernest Hemingway during his lifetime. For it, he won the Pulitzer Prize for Fiction in 1953 and it undoubtedly contributed to the Nobel Prize for Literature he was awarded in 1954.

The novel tells the story of Santiago, an old and experienced fisherman who embarks on a grueling three-day battle when he finally manages to catch a huge marlin. The Old Man and the Sea is considered one of the masterpieces of universal literature that has captivated readers around the world for decades . Its message about perseverance, dignity, and the search for life’s meaning is still relevant today. The novel is a must-read for anyone interested in literature and human nature.

4

In Cold Blood , Truman Capote (1965)

Image: Brandi Redd

On November 15, 1959, in a small Kansas town called Holcomb, the four members of the Clutter family, a married couple and their two teenage children, were savagely murdered by Dick Hickcock and Perry Smith.

Based on these gruesome events, the American novelist Truman Capote managed to turn around his career as a storyteller by writing In Cold Blood , the novel that definitively established him as one of the great authors of twentieth-century American literature. This book catapulted him as the pioneer of the New Journalism literary movement , a non-fiction genre that became popular in the 1960s for narrating stories based on real events.

5

The Catcher in the Rye , J. D. Salinger (1951)

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The Catcher in the Rye , written by the great J. D. Salinger, is a contemporary novel that has become a classic of modern literature. At the time of its publication in 1951, it provoked numerous controversies for its provocative language and its unabashed portrayal of teenage struggles, such as sexuality, the loss of innocence, and the transition to adulthood.

The Catcher in the Rye could be framed within the Bildungsroman —a literary genre that focuses on the psychological and moral growth of the protagonist. It follows Holden Caulfield, a teenager who, after being expelled from school, gets lost in New York trying to find his way in the world. The novel is rich in symbolism and themes , and the literary style and narrative technique are unique and exceptional.

6

American Pastoral , Philip Roth (1997)

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Published in 1997, American Pastoral is the novel that earned Philip Roth the Pulitzer Prize and is the first in the well-known "American Trilogy", a series of novels narrated by Nathan Zuckerman, the author's alter ego. With the Vietnam War as a backdrop, this book is a lucid tale that questions American values during the end of the happy sixties.

In American Pastoral we find Roth at his best: deep, intense, incisive, magnificent . His ability to build a universe of complex characters and dig into their psychologies is astounding and overwhelming. Few writers have managed to capture the contradictions of American society as he has done.

7

Beloved , Toni Morrison (1987)

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Beloved , published in 1987 by Nobel Prize winner Toni Morrison, takes place in the aftermath of the American Civil War . The novel tells the story of an African-American slave, Margaret Garner, who escapes from Kentucky to Ohio, a free state.

Magic realism runs throughout the entire book and manifests through the ghostly presence of Beloved's character. Morrison uses this technique to explore collective memory and the persistence of the past . The novel is considered a masterpiece of contemporary literature and has been acclaimed for its innovative writing style and its exploration of sensitive subjects such as slavery, freedom, identity, and memory.

8

On the Road , Jack Kerouac (1957)

Image: Daria Kraplak

On the Road is a semi-autobiographical novel in which Jack Kerouac recounts a series of trips he made across the United States and Mexico with his friend Neal Cassady. Inspired by his passion for jazz, Kerouac developed the idea of a book that would be a great improvised prose solo . He wrote it on his typewriter on a long, single roll of paper in just three weeks.

A cornerstone of the so-called "Beat Generation," On the Road was published in September 1957, after 6 years of delay due to the publisher's reservations about the explicit contents. At the time, this emblematic book had a major impact, especially on the younger readers of the 60s. Today, On the Road is still considered one of the great American novels of the 20th century for capturing the rebellious spirit of an entire generation.

9

The Heart is a Lonely Hunter , Carson McCullers (1940)

Image: Faith Enck

The Heart is a Lonely Hunter is a literary masterpiece that continues to resonate in the hearts of readers, even though it was published more than 60 years ago. Set in a small southern town, it tells the story of a group of people who have in common the rejection of a society that ignores them.

This is Carson McCullers' first novel, written when she was only twenty-three years old. She masterfully captures the essence of loneliness and the search for human connection in a way that transcends time. With a moving narrative and unforgettable characters, the novel has received critical acclaim and has earned a prominent place in literary history.

10

The Grapes of Wrath , John Steinbeck (1939)

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We couldn't leave The Grapes of Wrath, 1940 Pulitzer Prize winner , out of this list. In this harrowing book, Nobel laureate John Steinbeck narrates the difficult journey of a family of farmers who, beset by hunger and misery, leave the fields of Oklahoma to reach the golden shores of California, the promised land.

First published in 1939, The Grapes of Wrath is a seminal work in American literature that explores the conflict between the rich and the poor and reflects the horrors of the Great Depression with sensitivity and sharp insight. Steinbeck's chronicle of the shameful mistreatment of 1930s families is perhaps the most "American" of all American classics.

1

Cruella De Vil

Image: Helena Lopes

The Disney adventure comedy One Hundred and One Dalmatians premiered in 1961, and since then, Cruella de Vil has been one of the most iconic villains in animated film history.

This wicked woman is ambitious and capable of doing anything to get new fur for her coats. With the help of her henchmen, she steals the Dalmatian puppies her friends Anita and Roger had refused to sell her. Anyone who hurts cute little puppies to make coats deserves to be on the podium of the most evil villains in history!

2

Jafar

Image: Boris Hamer

Conspiracy and ruthlessness define any bad guy, and _Aladdin_’s villain is no exception. Jafar is capable of destroying anyone who stands in his way to gain more power.

Posing as an honest man, this evil sorcerer takes advantage of his role as the right hand of the Sultan of Agrabah and attempts to marry Princess Jasmine. His true intention, in fact, is to take over her father’s kingdom. If these traits don’t convince you that he is a true villain, just look at how he treats his sidekick, the charismatic parrot Iago.

3

Shan-Yu

Image: Stijn Dijkstra

Shan Yu is the main villain of the Disney movie Mulan (1998). This ruthless leader of the Huns is determined to conquer China. He and his army invade the land to prove his superiority to the emperor.

Cunning and sadistic, Shan-Yu feels no remorse when it comes to taking a life. Luckily, the brave Mulan manages to defeat him and ultimately saves the emperor.

4

Ursula

Image: Brian McGowan

Her tentacles and terrifying appearance are enough to make any child tremble. Ursula, the villain in The Little Mermaid (1989), uses magic to "help" others, although her deals are deceitful and become impossible to accomplish.

Ariel, the protagonist of this story, makes a deal with Ursula, who promises to turn her into a human for three days in exchange for her beautiful voice. If Ariel receives a "true love's kiss," she can be human forever. Despite the villain's attempts to make Ariel fail, she manages to keep her part of the deal by making Prince Eric fall in love with her.

5

Scar

Image: Brian McGowan

In The Lion King (1994), the second heir to the throne becomes one of the most ruthless villains when he murders his own brother and attempts to do the same to his nephew, Simba.

Although Scar only succeeds in causing Mufasa's demise, he convinces his nephew that it was his fault and that he must leave the kingdom forever. Scar orders the hyenas to destroy Simba, but what the evil lion could never have imagined is that the little boy would survive and return to avenge his father's death.

6

Queen Grimhilde

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Queen Grimhilde, better known as the Evil Queen, is the wicked stepmother in the 1937 film Snow White and the Seven Dwarfs . She is considered the first Disney villain.

Obsessed with being the most beautiful in the whole kingdom, she plots to have her stepdaughter —and competition— eliminated and demands Snow White’s heart. She even uses witchcraft to transform into an old lady, which allows her to give a poisoned apple to the naive princess. Can you think of anything more terrifying?

7

Gaston

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In the beginning, the Beast is presented as an irascible and cruel monster, but the real villain of Beauty and the Beast (1991) is Gaston.

The arrogant hunter is determined to marry Belle, even if it has to be by force. This obsession turns him into a ruthless being, capable of doing anything to have his love reciprocated. Luckily, Bella has no time to waste with this evil kind of man.

8

Maleficent

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When it comes to villains, no one can match Maleficent. The powerful sorceress doesn't hesitate when it comes to summoning an army of monsters or using her magic for revenge.

In Sleeping Beauty (1959), Maleficent curses Princess Aurora with eternal sleep for not being invited to her christening. This villain is so popular that Disney has produced two live-action movies with Angelina Jolie in the lead role: Maleficent (2014) and Maleficent: Mistress of Evil (2019).

9

Captain Hook

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One of Disney's most iconic villains is, without a doubt, Captain Hook. In Peter Pan (1953), the ruthless pirate seeks to destroy the Boy Who Would Never Grow Up for being responsible for the loss of his hand and also for taunting him every time their paths cross.

Despite his inherent evilness, we can't help but laugh at Captain Hook and his irrational fear of the crocodile that ate his hand. A villain with such a weakness can't be all that terrifying, don't you think?

10

Lady Tremaine

Image: Gary Cooper

Wicked stepmothers are a classic of Disney movies and the one in Cinderella (1950) is perhaps one of the most iconic. Lady Tremaine made us shudder every time she appeared from the shadows stroking her cat, Lucifer.

To be fair, this stepmother might not have been so scary without the presence of her equally evil daughters, Anastasia and Drizella. Dead jealous, the three women make life miserable for poor Cinderella, relegated to serving and being exploited in her own home after the passing of her father. Perhaps the most terrifying thing about Lady Tremaine is that she successfully manages to inflict extreme suffering on Cinderella without laying a finger on her.

11

Governor Ratcliffe

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Governor Ratcliffe is the main villain in Disney's historical drama Pocahontas (1995). This money-hungry English settler is greedy, and he doesn't trust the "savages." He sends his men to attack them because he believes they're hiding a gold treasure.

Even when they discover that the Native Americans don't possess the riches, he still declares war on them. In a confrontation, Ratcliffe fires his musket at Chief Powhatan, but Captain John Smith —Pocahontas' love interest— takes the shot to save him. Finally, the settlers turn on Ratcliffe and arrest him for hurting their comrade.

12

Queen of Hearts

Image: Laine Cooper

Although the Queen of Hearts appears only at the end of Disney's version of Alice in Wonderland (1951), it is enough for us to notice the fear she inflicts on her subjects. This villainess is a childish, hotheaded monarch whose catchphrase is "Off with their heads!"

After feeling humiliated during a game of croquet, she loses her temper. The king convinces her to put Alice on trial before cutting off her head. Nothing seems to go right for the girl who must escape to save her life. Luckily, she finally realizes that she is in a dream and manages to wake up before she is caught by the tyrant queen.

1

Alcatraz wasn’t always a prison

Image: Maxim Babichev

Before housing America’s most dangerous criminals, Alcatraz served as a military fort. In 1850, President Millard Fillmore designated the island as a military reservation, and by the Civil War, it held prisoners of war. Its strategic location in San Francisco Bay made it ideal for defense. It wasn’t until 1933 that it officially became a federal penitentiary. Over the years, its role shifted dramatically, but its reputation as an isolated fortress remained constant.

2

Prisoners built their own cells

Image: Oxana Melis

Talk about a tough day on the job! When Alcatraz transitioned from a military prison to a federal one, military prisoners were put to work constructing their own confinement. Between 1909 and 1911, they reinforced the existing structures to prepare for the worst of the worst. By the time the Department of Justice took over, the prison was ready to house America’s most notorious inmates. Imagine building the very walls that would later trap you inside!

3

Guards and their families lived on the island

Image: Tyler Rutherford

Alcatraz wasn’t just a prison; it was also home to families. The guards and their families lived in houses and apartments on the island, creating a tight-knit community. Children took a ferry to school in San Francisco every day and played safely away from the prison yard. Some even recall watching movies in the recreation hall while criminals like Al Capone were locked up just a few feet away. Life on Alcatraz wasn’t all gloomy for those outside the cells.

4

No executions took place on Alcatraz

Image: Rita Morais

Despite its reputation, Alcatraz never had an execution chamber. While prisoner violence did lead to some deaths, executions were not carried out on the island. Inmates sentenced to death were transferred to facilities like San Quentin. That didn’t make life any easier in Alcatraz; many prisoners still feared the harsh conditions and inescapable isolation of The Rock.

5

The Pacific Coast’s first lighthouse was on Alcatraz

Image: Bruce Warrington

Before it became infamous for its prison, Alcatraz played a vital role in maritime safety . In 1854, it became home to the first lighthouse on the Pacific Coast, guiding ships through the often foggy San Francisco Bay. Though a larger lighthouse replaced it in 1909, the original helped countless sailors navigate the treacherous waters surrounding the island. Today, it stands as a historic landmark, reminding visitors of Alcatraz’s earlier days.

6

No inmate officially escaped

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While Hollywood loves a good prison break story, no prisoner ever successfully escaped Alcatraz, at least not officially. The closest attempt came in 1962 when three inmates, including Frank Morris, disappeared after digging their way out using spoons. Their bodies were never found, leading to decades of speculation. Did they drown in the freezing bay or make it to freedom? The mystery remains unsolved.

7

Alcatraz shut down due to high costs

Image: Jack Walker

Despite its reputation as America’s toughest prison, Alcatraz didn’t close due to security issues: It was just too expensive to maintain . The constant exposure to salt water eroded the buildings, and the cost of housing each inmate was three times higher than in other federal prisons. By 1963, the government decided to shut it down. The island was abandoned for years before turning into the tourist attraction it is today.

8

Some inmates requested transfers to Alcatraz

Image: Mylo Kaye

Despite its harsh image, some prisoners actually wanted to be transferred to Alcatraz. The prison provided single cells, which meant no cellmates to fight with . It also had some of the best food in the federal system because officers believed that well-fed inmates were less likely to cause trouble. For some, the strict routine and isolation were preferable to overcrowded, violent prisons elsewhere.

9

Alcatraz was named after pelicans

Image: Mollie Sivaram

Before it became synonymous with crime and punishment, Alcatraz was simply an island full of birds. Spanish explorer Juan Manuel de Ayala named it La Isla de los Alcatraces in 1775, which translates to "Island of the Pelicans." Over time, the name was anglicized to Alcatraz. Even today, the island remains a haven for seabirds, making it a birdwatcher’s paradise.

10

Alcatraz was never packed to capacity

Image: Kenny Eliason

Alcatraz was never overflowing with inmates . The prison had a maximum capacity of 336, but on average, only about 260 prisoners lived there at any given time. Sometimes, there were as few as 222. This was intentional—authorities wanted to ensure strict control over the inmates. It’s a far cry from the overcrowded prisons we hear about today.

11

Warm water showers had a hidden purpose

Image: David Castellón

Prisoners at Alcatraz were given warm water showers, not necessarily out of kindness, but as a security measure. Authorities believed that if inmates were used to warm water, they’d be less likely to brave the freezing bay in an escape attempt. Whether it worked or not is up for debate, but it certainly added another layer to Alcatraz’s infamous reputation.

12

Officers and inmates tended the gardens

Image: Maxim Babichev

Alcatraz wasn’t all cold concrete and iron bars; there were actually gardens on the island. Prison officers and even some inmates planted flowers and hardy greenery to make the island more livable. The tradition continued for decades, and today, the National Park Service maintains the Gardens of Alcatraz . It’s a surprising touch of beauty in a place best known for its harshness.